"Mad Sam" DeStefano: The Mob’s Marquis de Sade

When FBI agents and members of the Chicago Police Department’s Organized Crime Unit showed up to monitor the mourners at "Mad Sam" DeStefano’s funeral, they were disappointed, but not surprised. The "puny" turnout, which included a 10-car caravan to the cemetery, only amplified what law enforcement had known for years: "Mad Sam" was despised by everyone who knew him.

DeStefano was born in 1909. In what would prove to be a fitting start to his vicious criminal career, DeStefano, at age 18, was convicted of raping a teenage girl and sent to prison for three years.

In 1932, as a member of Chicago’s infamous "42 Gang," he was shot during an attempted burglary of a grocery store. By 1933 he was back in prison, this time for robbing a bank in New Lisbon, Wis. DeStefano was captured while climbing a tree to escape after the getaway car broke down and the robbers took off into the woods. He served 11 years before his release in 1944.

Three years later he was in Leavenworth Federal Penitentiary serving time for selling counterfeit sugar ration stamps. While there he met Chicago mob heavyweights Paul Ricca and Louis Campagna. After his release, DeStefano worked as a laborer for the city of Chicago. In 1949, he passed the civil service test to become a garbage dump foreman, lying on the application about his criminal past. When the falsification was discovered in 1952, the city refused to file charges.

In William Brashler’s The Don: The Life and Death of Sam Giancana, he gives this description of DeStefano: "The mob was full of psychopaths and morons, and keeping order among them was a challenge to the mettle of any boss, be he an elderly don like Paul Ricca, or a power broker like Giancana. Nobody tested the patience and discipline of both men more than Sam DeStefano, a freelance juice-loan operator and terrorist who was the pre-eminent clown prince of the Chicago outfit, a buffoon with no equal. …DeStefano through the years had somehow gained the favor of Ricca and Giancana, a standing that kept him alive. For nobody made more enemies, or talked louder, than DeStefano, the mad hatter."

DeStefano’s brother, Michael, who also worked for the city, developed a drug habit and sources said Giancana wanted him out of the way. Sam carried out the murder himself by stabbing his brother to death. He then stripped the body and washed it with soap and water "to cleanse his brother’s soul."

Although many people considered him crazy, DeStefano was a sharp businessman. After a big score from a bank robbery in the early 1930s, he purchased an apartment building with 24 suites. He used the rent money to help support local politicians. Over the years, as his contributions increased, so did the number of people on Sam’s payroll, which, in addition to political figures, included judges and police officers.

By the mid-1950s, DeStefano boasted that with his connections, there wasn’t any case he couldn’t fix. Standard fees for fixing cases were; $1,500 for assault and $800 for robbery. He once fixed an "open and shut" first-degree murder indictment for $20,000. He became so well known to police officers who were on the take that it was not unusual for an arrested criminal to be driven to Sam’s house, where the police would be paid off and the criminal freed and put "on juice for the fix."

It was said that if DeStefano promised a fix, he delivered. If a defendant lost in court, DeStefano paid the appeal costs out of his own pocket. By the late 1950s though, DeStefano knew the big dollars were in loansharking. His clientele included borrowers from all levels of Chicago society. The upper levels included politicians and attorneys, while petty crooks borrowed money just to party for the evening or to cover an unexpected expense that came due. Other times the clients were holdup men who needed to finance a robbery. DeStefano profited the most from small-time borrowers where his loans carried a 20 to 25 percent interest rate. Sam found that when these people went into hiding, they were the easiest to find and frighten because wives were always eager to help the collectors find their husbands. One collector was quoted, "I’d like to have a dollar for every wife that set her husband up for me. Hell, I wouldn’t have to worry anymore."

There were many stories about DeStefano’s viciousness. Peter Cappelletti, one of his collectors, once took off with $25,000 of Sam’s money. DeStefano found him in Milwaukee and brought him back to Chicago. He took him to Mario’s Restaurant in Cicero, which was owned by his brother. In the basement, DeStefano, his brother, and collectors Charles Crimaldi and Sam Gallo stripped Cappelletti and handcuffed him to a hot radiator. Over the next 75 hours Cappelletti was brutally kicked and beaten. DeStefano then decided to have a party at the restaurant. The invitation list included judges, politicians, police officers, several of Sam’s mob friends, and Mrs. Cappelletti. After dinner, DeStefano made a speech in front of the group telling how Cappelletti had stolen from him and what a big heart he had for letting him live. As he was expounding, Crimaldi, Gallo, and Mario DeStefano went to the basement. There they gave Cappelletti yet another beating and then the three urinated on him. When this was done, they took him upstairs just as Sam was completing his speech and pushed him, naked, burned, bloodied, and dripping with urine into the room in front of his wife.

The vicious stories weren’t limited to DeStefano’s criminal activities. Once, after an argument with his wife, Anita, he went out and abducted a black man off the street. Taking him home, he forced his wife Anita and the man to perform oral sex on each other at gunpoint.

In the wake of the 1957 Appalachian Conference, Hoover began to focus on the organized crime problem in the United States. One of the objectives for his FBI agents was to turn members of organized crime into informants. This effort was called the Top Hoodlum Program. In Chicago, agent William F. Roemer, Jr., a six-foot two inch, former Marine and four-time boxing champ at Notre Dame, would try his hand at recruiting DeStefano for this program. Roemer, who had a bit of an ego himself and later authored five books about the mob (two of which were fictionalized accounts), discussed DeStefano is his first book, Roemer: Man Against the Mob: "About this time I got to know Mad Sam DeStefano, the worst torture-murderer in the history of Chicago. He was a sadistic, arrogant, swaggering thug of the worst order, responsible for scores of killings, almost all by his own hands. I had a long series of confrontations with this beast, and looking back I must admit I enjoyed every one."

When Bill Roemer first met DeStefano, Roemer went to his home to inquire about the murder of Arthur Adler, a local restaurant owner who fell behind in his loanshark payments. Roemer was certain that "Mad Sam" had caused Adler’s death. DeStefano met Roemer and his partner at the door wearing a pair of pajamas with the fly open and his penis hanging out. DeStefano walked around his mirrored living room, holding his penis and staring at it in the mirror. Roemer blurted out, "You killed Artie Adler." This diverted DeStefano’s attention away from his penis and he called for his wife, Anita, his three children, and their friends to come downstairs. Once assembled, he screamed at them, "These two gentlemen are FBI agents. They have come out here to accuse me of killing Arthur Adler! I cry out to God up above! If I am guilty of killing Arthur Adler, may God come down, right now, and put cancer in the eyeballs – of you, and you, and you," he shouted, pumping his finger in each one of their faces.

As Roemer and his stunned partner drove back to their office in complete silence, Roemer decided he would attempt to turn DeStefano. Roemer subsequently made several return trips to DeStefano’s home. Each time, Sam’s wife, Anita, would prepare breakfast and coffee for him. Word of these morning meetings was passed on to street detectives, most likely from hoods who had heard about them directly from DeStefano.

One day Roemer received a call from Bill Duffy of the Chicago Police Department’s Intelligence Division. "Roemer," Duffy asked, "have you been going out to Sam DeStefano’s house?"

Roemer, who never discussed informants or people he was trying to turn, inquired, "Why do you ask, Bill?"

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With the purpose of writing about true crime in an authoritative, fact-based manner, veteran journalists J. J. Maloney and J. Patrick O’Connor launched Crime Magazine in November of 1998. Their goal was to cover all aspects of true crime: Read More